Triaryl-methane dyes from tetraalkyl-diamino-benzophenone and arylated-ethylene-diamines



Patented May 24, 1927.

UNITED STATES PATENT" OFFICE.

HEINRICH POLIKIER, OF LEIIPZIG,'.AND HERBERT HKHLE, OF DESSAU-ZIEBIGK,GER.

MANY, ASSIGNORS TO I. G. FARBENINDUSTRIE AKTIENGESELLSCHAFTQOF FRANK-FORT-ON-THE-MAIN, GERMANY.

TRIARYL-METHANE nYEs FROM TETRAALKYL-DIAMINO-BENZOPHENONE ANDARYLA'TED-E'rHYLENE-DIAMINES.

No Drawing. Application filed May 6, 19 26, Serial No. 107,227, and inGermany March 14, 192 5.

The invention relates to valuable violet dyestufl'sof the triarylmcthaneseries made by condensing a tetraalkyllAt' diaminobenzophenone with anarylated ethylene- 5 diamine, in which there is no substiruent m the.aryl-residue in para-position to the mtrog'en. The arylenediaminesapplied for condensation correspond to the general formula:

X representing hydrogen, alkyl or aralkyl.

The reaction occurs between equal molecular proportions with formationof a dyestufi of the general constitution:

C-ary1-NOHz-CH;-N-aryl (alkyDzN-GeHA X representing hydrogen, alkyl orarallzyl. The new dyestuifs are characterized by remarkable clarity,colour strength and fastness to washing. In their other dyeingproperties they approximate the Victoria blue group (see Schultz,Farbstofi'tabellen, 6. edition, 1. Vol. No. 558 and 559).

The following examples illustrate the in- ;vention without limiting it,the parts being by Weight: I

l. 27 parts of tetramethyllAr-diaminobenzophenone, 2 k parts ofdimethyldiphenylethylenediamine and 7 parts of toluene are meltedtogether. To the mixture cooled to 60 C. are added 18 parts'ofphosphorusoxychloride and the mass is stirred on the water bath until itbecomes solid. It is then dissolved in 500 parts of water and thedyestutf is precipitated from the solution by adding sodium acetate andsodium chloride. It separates in the form of a' resin having a goldenlustre which can be dried and ground. It dyes cotton mordanted withtannin, or wool, Violet shades.

2. 27 parts of tetrameth l-AJ-diaminobenzop'henone, 27 parts ofdiethyldiphen'ylethylenediamine and 7 parts of toluene are meltedtogether. At about 60 C. there are added 18 parts of phosphorusoxychloride and the remaining operations resemble those described inExample 1. The dyestuif produced is of a somewhat more blue tint thanthat of the dyestuff of Example 1.

3. 27 parts of tetramethyl-4.4-diaminobenzophcnone, 39 parts of dibenJyldiphenylethylenediamine and 15 parts oi toluene are heated in themanner described in the previous examples with 18 parts ofphosphorusoxychloride. During the working up the dyesfuft separates inapure and solid form. after its solution in hot water. has been stirredfor some time. It dyes tannin-mordanted cotton. or wool. blueviolet/shades.

By sulphonation it is converted into a dyestutt' which dyes wool in anacid bath verv clear blue violet tints. 4. 27 parts oftetra1netl1yl-4.4'-diaminohenzophenone. 25 parts ofdi-ortho-tolylethylenediamine, 10 parts of tolueneand 18 parts ofphosphorus-oxychloride are worked up as described in Example 1. From thesolution obtained by stirring the product in hot water the dyestufiiseparates after the correspond to the general formula:

(x representing hydrogen, alkyl or aralkyl) and which are substantiallyidentical with the dyestuffs manufactured bycondensing equal molecularproportions of a tetra alkyl-44'-diaminobenzophenone 'arylatedethylenediamine corresponding to the general formula:

(X representing hydrogen, alkyl or aralkyl) havingno substituent in thearyl resi due in para-positi0n to the nitrogen.

2. The herein-described new violet dyestuffs of the triarylemethaneseries which correspond to the general formula:

(X representing hydrogen, alkyl or aralkyl),

and which are substantially identical with the dyestuffs manufactured bycondensing equal molecular proportions of tetramethyl-4-4J-diaminobenzophenone with an arylated ethylenediamine correspondingto the general formula:

(X representing hydrogen, alkyl or aralkyl) having no substituent in thearyl residue in para-position'to the nitrogen.

3. The herein-described new violet dyestufis of the triarylmethane seies which correspond to the general formula:

(CHa)I-N-CoH4 (X representing hydrogen, alkyl or aralkyl), and which aresubstantially identical with the dyestuffs manufactured by condensingequal molecular proportions of tetramethyl-4.4-diaminobenzophenone witha with an diphenylethylenediamine corresponding to the general formula:

N-OHa-CH:-N I (X1 representing hydrogen, alkyl or aral- 4. Theherein-described new violet dyestuffs of the triarylmethane series whichcorrespond to the general formula:

(1% representing hydrogen, alkyl or phestuff of the triarylmethaneseries which corresponds to the formula:

which dyestuff is substantially identical with the dyestuif manufacturedby condensing molecular proportions of tetramethyl-4fldiaminobenzophen0ne .with diphenyldlethylethylenediamine.

In testlmony whereof we affix our signatures.

HEINRICH PQLTKIER. HERBERT 5. The herein-described new violet dye- 70

